EP1220661A2 - Systeme therapeutique transdermique permettant de delivrer de l'acide acetylsalicylique et/ou de l'acide salicylique - Google Patents

Systeme therapeutique transdermique permettant de delivrer de l'acide acetylsalicylique et/ou de l'acide salicylique

Info

Publication number
EP1220661A2
EP1220661A2 EP00966096A EP00966096A EP1220661A2 EP 1220661 A2 EP1220661 A2 EP 1220661A2 EP 00966096 A EP00966096 A EP 00966096A EP 00966096 A EP00966096 A EP 00966096A EP 1220661 A2 EP1220661 A2 EP 1220661A2
Authority
EP
European Patent Office
Prior art keywords
therapeutic system
transdermal therapeutic
group
matrix
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP00966096A
Other languages
German (de)
English (en)
Other versions
EP1220661B1 (fr
Inventor
Hanshermann Franke
Heinrich Kindel
Gerd Hoffmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LTS Lohmann Therapie Systeme AG
Original Assignee
LTS Lohmann Therapie Systeme AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LTS Lohmann Therapie Systeme AG filed Critical LTS Lohmann Therapie Systeme AG
Publication of EP1220661A2 publication Critical patent/EP1220661A2/fr
Application granted granted Critical
Publication of EP1220661B1 publication Critical patent/EP1220661B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A61K31/612—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid
    • A61K31/616—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid by carboxylic acids, e.g. acetylsalicylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • A61K9/7061—Polyacrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin

Definitions

  • Transdermal therapeutic system for the delivery of acetylsalic acid and / or salicylic acid
  • the invention relates to a transdermal therapeutic system which enables the delivery of acetylsalicylic acid or salicylic acid, or both active ingredients together, to the skin. It also relates to a method for producing such a system.
  • the active ingredient acetylsalicylic acid is widely used as an analgesic, antipyretic, anti-inflammatory and to inhibit platelet aggregation.
  • Acetylsalicylic acid interferes with the prostaglandin metabolism and thereby suppresses the formation of mediator substances, which play a central role in pain and inflammation. This is caused by inhibition of a cyclooxygenase, an enzyme in the prostagglatin-biosynthetic pathway.
  • the active ingredient acetylsalicylic acid is therefore included in the group of so-called COX-2 inhibitors.
  • Salicylic acid is also anti-inflammatory, and is also used due to its antiseptic and anticoagulant properties.
  • the object of the present invention was therefore to provide a transdermal dosage form for the active ingredients acetylsalicylic acid and salicylic acid, which enables a sufficiently high flux of active ingredients in vivo and which can be produced inexpensively by means of conventional manufacturing processes.
  • TTS transdermal therapeutic system
  • the TTS according to the invention is characterized in that it contains at least one component from the group of pyrrole derivatives and at least one component from the group of terpenes.
  • the joint presence of constituents from the two groups leads to an unexpected increase in the transport of active substances through the skin in vivo (cf. Tables 1 and 1).
  • 2-pyrrolidone As a representative from the group of pyrrole derivatives, 2-pyrrolidone has proven to be particularly effective. But other pyrrole derivatives can also can be used richly, and two or more compounds from this group can also be used together.
  • Limonene is particularly suitable as a representative of the Terpe ⁇ e group, but natural terpene mixtures whose main constituent is limonene can also be used with advantage.
  • other terpenes, individually or in combination, can also be used as part of the TTS according to the invention.
  • the components from the group of the pyrrole derivatives in a concentration range of 0.1-15%, preferably from 2 to 10%, and the components from the Group of terpenes are used in a concentration range of 1-30%, preferably 10-20%, each based on the total mass of the matrix.
  • the TTS according to the invention preferably have a layered structure with at least one polymer matrix layer. This can also perform the function of the drug reservoir. In individual cases it can also be advantageous if the TTS according to the invention have two or more matrix layers. These can have different active substances or different active substance concentrations. Furthermore, the individual matrix layers can also differ with regard to their content of enhancers or other additives.
  • the matrix layer can also be designed with a pressure-sensitive adhesive in order to enable the patch to be attached to the skin.
  • the reservoir containing the active substance itself is not or not sufficiently pressure-sensitive adhesive, it can be connected to a special pressure-sensitive adhesive device which ensures permanent contact of the system with the skin.
  • the same materials can be used for this as for the polymer matrix of the active substance reservoir.
  • the reservoir can be provided with a control membrane which controls the release of the active ingredient to the skin.
  • the polymer matrix layers of the TTS according to the invention are preferably built up from polymers selected from the group consisting of the polyacrylic acid esters and their copolymers, polymers based on (meth) acrylate, ethylene vinyl acetate copolymers, polyisobutylenes, polyterpenes, cellulose derivatives, rubbers, synthetic rubbers and hot melt adhesive.
  • polymers selected from the group consisting of the polyacrylic acid esters and their copolymers, polymers based on (meth) acrylate, ethylene vinyl acetate copolymers, polyisobutylenes, polyterpenes, cellulose derivatives, rubbers, synthetic rubbers and hot melt adhesive.
  • acrylate-based polymers copolymers of 2-ethylhexyl acrylate, vinyl acetate and acrylic acid with or without crosslinking agents are preferred.
  • the poly-methacrylates used are mainly copolymers based on dimethylaminomethacrylate and neutral methacrylic acid
  • At least one matrix layer contains polymer constituents which are selected from the group of substituted celluloses, preferably methyl or ethyl celluloses.
  • at least one matrix layer contains esters of the hydrogenated rosin, preferably its methyl or glycerol ester.
  • the mechanical properties of the TTS can be influenced by the selection of the matrix polymers and the other matrix components.
  • the layered structure of the TTS according to the invention also comprises an impermeable backing layer and a removable protective layer.
  • a backing layer are polyesters, which are notable for their particular strength and diffusion resistance, but moreover almost any other skin-compatible plastics, such as B. polyvinyl chloride, ethylene vinyl acetate, vinyl acetate, polyethylene, polypropylene, cellulose derivatives and many others.
  • the backing can be provided with an additional layer, e.g. B. by vapor deposition with metals or other diffusion-blocking additives such as silicon dioxide, aluminum oxide or similar substances known to the person skilled in the art.
  • the removable protective layer as for the backing layer, provided that they are protected by a suitable surface treatment such as. B. Siliconization were made removable.
  • other removable protective layers such as paper treated with tetrafluoroethylene, cellophane, polyvinyl chloride or the like can also be used.
  • auxiliaries or additives can be added.
  • Plasticizers and permeation accelerators are particularly suitable.
  • tackifiers, stabilizers, fillers and carriers can also be added.
  • the pharmaceutically acceptable additives that are suitable for this are known to the person skilled in the art.
  • Plasticizers Compounds from the group of hydrocarbons, alcohols, carboxylic acids and their derivatives, ethers, esters or amines are preferably used as plasticizers, it also being possible to use individual plasticizer compounds in combination with one another.
  • a preferred embodiment of the invention provides a plasticizer content of 0-30%, preferably 5-20%, in each case based on the total mass of the matrix.
  • a further preferred embodiment is characterized in that the TTS contains a natural or partially synthetic triglyceride or a mixture of these triglycerides in a concentration range of 0-30%, preferably in the range of 5-20%, based on the total mass of the matrix.
  • TTS permeation accelerators from the group of polyoxyethylene derivatives and non-ionic surfactants, preferably sorbitan fatty acid esters, are
  • concentration of the permeation accelerator or accelerators is in a range of 0-5%, preferably 1-3%, based on the total mass of the matrix.
  • the active ingredient acetylsalicylic acid or salicylic acid is usually dispersed or dissolved in one or more polymer matrix layers of the TTS according to the invention in as homogeneous a distribution as possible.
  • the active ingredient can also be present in a bag-shaped reservoir which is filled with a liquid, highly viscous, semi-solid or thixotropic matrix which contains the active ingredient. It is particularly advantageous if the semi-solid or thixotropic active substance reservoir contains a gel former.
  • the back of the bag facing away from the skin must be impermeable to active substances, the side facing the skin must be permeable to active substances.
  • an active substance-permeable membrane can take over the control of the active substance release.
  • the highest possible active substance concentration in the active substance-containing layers is preferably sought, although it should be noted that the stability of the system can be impaired if the concentrations are too high.
  • active substance concentrations in the range from 5-75%, in particular from 15-45%, are therefore preferred, based on the total mass of the layers containing the active substance.
  • laminate coating 1 2-pyrrolidone and ASA were dispersed in a polyacrylate adhesive. A suspension was formed which was coated on a 100 ⁇ m PET film (release liner / protective layer). After drying, this laminate was covered with an HDPE film (intermediate liner), rolled up and stored protected from moisture. This dried laminate is referred to as laminate coating 1.
  • Oleum citri was processed with a polymethacrylate (Plastoid ® B) to a homogeneous viscous solution and coated on a 19 ⁇ m PET film (backing layer), which results in laminate coat 2 (moist).
  • Pullastoid ® B polymethacrylate
  • a corresponding formulation without 2-pyrrolidone was used as a comparative example (No. 8271508).
  • the permeation rates through human skin were determined using Franz diffusion cells.
  • the values contained in the table columns represent the amount of active ingredient released per unit area (cm 2 ) (in ⁇ g).
  • FIG. 1 shows a graphical representation of the data from Table 1.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Materials For Medical Uses (AREA)

Abstract

La présente invention concerne un système thérapeutique transdermique, contenant de l'acide acétylsalicylique et/ou de l'acide salicylique et se présentant sous forme de pansement. Ledit système présente une couche de support, un réservoir de principe actif qui est relié à ladite couche de support, une membrane qui commande la délivrance du principe actif en l'absence d'autres mécanismes de commande, un dispositif adhésif qui permet de fixer le système sur la peau, ainsi qu'une couche de protection qui peut être détachée avant l'application. Le système selon l'invention se caractérise en ce qu'il contient au moins un composant issu du groupe des dérivés de pyrrole et au moins un composant issu du groupe des terpènes.
EP00966096A 1999-10-13 2000-09-30 Systeme therapeutique transdermique permettant de delivrer de l'acide acetylsalicylique et/ou de l'acide salicylique Expired - Lifetime EP1220661B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19949202A DE19949202A1 (de) 1999-10-13 1999-10-13 Transdermales therapeutisches System zur Abgabe von Acetylsalicylsäure und/oder Salicylsäure
DE19949202 1999-10-13
PCT/EP2000/009617 WO2001026637A2 (fr) 1999-10-13 2000-09-30 Systeme therapeutique transdermique permettant de delivrer de l'acide acetylsalicylique et/ou de l'acide salicylique

Publications (2)

Publication Number Publication Date
EP1220661A2 true EP1220661A2 (fr) 2002-07-10
EP1220661B1 EP1220661B1 (fr) 2005-11-16

Family

ID=7925396

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00966096A Expired - Lifetime EP1220661B1 (fr) 1999-10-13 2000-09-30 Systeme therapeutique transdermique permettant de delivrer de l'acide acetylsalicylique et/ou de l'acide salicylique

Country Status (8)

Country Link
EP (1) EP1220661B1 (fr)
JP (1) JP4938949B2 (fr)
AR (1) AR026038A1 (fr)
AT (1) ATE309792T1 (fr)
AU (1) AU7660900A (fr)
DE (2) DE19949202A1 (fr)
ES (1) ES2253257T3 (fr)
WO (1) WO2001026637A2 (fr)

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USRE44145E1 (en) 2000-07-07 2013-04-09 A.V. Topchiev Institute Of Petrochemical Synthesis Preparation of hydrophilic pressure sensitive adhesives having optimized adhesive properties
US20050215727A1 (en) 2001-05-01 2005-09-29 Corium Water-absorbent adhesive compositions and associated methods of manufacture and use
WO2002087645A1 (fr) 2001-05-01 2002-11-07 A.V. Topchiev Institute Of Petrochemical Synthesis Compositions d'hydrogel
US8206738B2 (en) 2001-05-01 2012-06-26 Corium International, Inc. Hydrogel compositions with an erodible backing member
US8840918B2 (en) 2001-05-01 2014-09-23 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Hydrogel compositions for tooth whitening
US8541021B2 (en) 2001-05-01 2013-09-24 A.V. Topchiev Institute Of Petrochemical Synthesis Hydrogel compositions demonstrating phase separation on contact with aqueous media
CA2453013C (fr) 2002-12-13 2011-02-15 Gary W. Cleary Dispositifs d'administration d'ingredients par voie percutanee, transdermique ou transmuqueuse ou par les muqueuses
US7888546B2 (en) 2003-07-03 2011-02-15 Corium International, Inc. Wound dressing, ingredient delivery device and IV hold-down, and method relating to same
WO2005074894A1 (fr) 2004-01-30 2005-08-18 Corium International Film a dissolution rapide pour la delivrance d'agent actif
MX2007001512A (es) 2004-08-05 2007-04-20 Corium Int Inc Composicion adhesiva.
CA2751884C (fr) 2009-01-14 2018-09-25 Corium International, Inc. Administration transdermique de tamsulosine
WO2011076401A1 (fr) 2009-12-23 2011-06-30 Holger Schankin Compositions pharmaceutiques sensiblement exemptes d'eau, contenant de l'acide acétylsalicylique
US20220265589A1 (en) * 2021-02-23 2022-08-25 Nanomed Skincare, Inc. Method of administering a dual therapeutic and cosmetic agent

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Also Published As

Publication number Publication date
DE19949202A1 (de) 2001-05-03
AU7660900A (en) 2001-04-23
JP2003511408A (ja) 2003-03-25
WO2001026637A2 (fr) 2001-04-19
AR026038A1 (es) 2002-12-26
EP1220661B1 (fr) 2005-11-16
JP4938949B2 (ja) 2012-05-23
ATE309792T1 (de) 2005-12-15
DE50011653D1 (de) 2005-12-22
WO2001026637A3 (fr) 2001-12-13
ES2253257T3 (es) 2006-06-01

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